Modified heterophasic polyolefin composition

ABSTRACT

A heterophasic polymer composition comprises a propylene polymer phase, an ethylene polymer phase, and a compatibilizing agent. The compatibilizing agent comprises (i) an acyclic carbon-carbon double bond having a first carbon atom and a second carbon atom, (ii) an electron withdrawing group directly bonded to the first carbon atom in the acyclic carbon-carbon double bond, and (iii) a second carbon-carbon multiple bond in conjugation with the acyclic carbon-carbon double bond, wherein the second carbon-carbon multiple bond is linked to the acyclic carbon-carbon double bond through the second carbon atom.

CROSS-REFERENCE TO RELATED PATENT APPLICATIONS

This application claims, pursuant to 35 U.S.C. §119(e)(1), priority toand the benefit of the filing date of U.S. Patent Application No.62/028,905 filed on Jul. 25, 2014, which application is herebyincorporated by reference in its entirety.

TECHNICAL FIELD OF THE INVENTION

The present invention is directed to heterophasic polyolefincompositions having increased melt flow rates, as well as high impactstrength and improved clarity. Of particular interest are modifiedpolypropylene impact copolymers.

BACKGROUND

The melt flow rate (MFR) of a polymer resin is a function of itsmolecular weight. In general, increasing the melt flow rate allows theresin to be processed at lower temperatures and to fill complex partgeometries. Various prior art methods of increasing the melt flow rateinvolve melt-blending the resin in an extruder with a compound capableof generating free radicals, such as a peroxide. The weight averagemolecular weight of the polymer is reduced and the MFR is increased.Increasing the melt flow rate by decreasing the molecular weight of thepolyolefin polymer, however, has been found in many cases to have adetrimental effect on the strength of the modified polymer. For example,decreasing the molecular weight of the polymer can significantly lowerthe impact resistance of the polymer. And this lowered impact resistancecan make the polymer unsuitable for use in certain applications or enduses. Accordingly, when extant technologies are utilized, one muststrike a compromise between increasing the melt flow rate andundesirably decreasing the impact resistance of the polymer. Thiscompromise often means that the melt flow rate is not increased to thedesired level, which requires higher processing temperatures and/orresults in lower throughputs.

A need therefore remains for additives and processes that can producepolymer compositions having an increased high melt flow whilepreserving, or even improving, the impact resistance of the polymer.

BRIEF SUMMARY OF THE INVENTION

The invention generally provides heterophasic polymer compositionscomprising a propylene polymer phase and an ethylene polymer phase. Acompatibilizing agent is also added to the compositions. The addition ofthe compatibilizing agent to the compositions has been observed topreserve, or even improve, the impact resistance of the polymercomposition when the melt flow rate of the polymer composition isincreased by the use of a free radical generator.

Thus, in a first embodiment, the invention provides a heterophasicpolymer composition comprising:

(a) a propylene polymer phase comprising propylene polymers selectedfrom the group consisting of polypropylene homopolymers and copolymersof propylene and up to 50 wt. % of one or more comonomers selected fromthe group consisting of ethylene and C₄-C₁₀ α-olefin monomers;

(b) an ethylene polymer phase comprising ethylene polymers selected fromthe group consisting of ethylene homopolymers and copolymers of ethyleneand one or more C₃-C₁₀ α-olefin monomers; and

(c) a compatibilizing agent, the compatibilizing agent comprising (i) anacyclic carbon-carbon double bond having a first carbon atom and asecond carbon atom, (ii) an electron withdrawing group directly bondedto the first carbon atom in the acyclic carbon-carbon double bond, and(iii) a second carbon-carbon multiple bond in conjugation with theacyclic carbon-carbon double bond, wherein the second carbon-carbonmultiple bond is linked to the acyclic carbon-carbon double bond throughthe second carbon atom.

In a second embodiment, the invention provides a heterophasic polymercomposition comprising a continuous phase comprising polypropylenepolymers selected from the group consisting of polypropylenehomopolymers and copolymers of propylene and up to 80 wt. % of one ormore comonomers selected from the group consisting of ethylene andC₄-C₁₀ α-olefin monomers and a discontinuous phase comprisingelastomeric ethylene copolymers having an ethylene content of from 8 to90 wt. % selected from the group consisting of copolymers of ethyleneand one or more C₃-C₁₀ α-olefin monomers, provided that the propylenecontent of the propylene polymer phase is greater than the propylenecontent of the ethylene polymer phase, wherein the composition furthercomprises propylene polymers bonded to ethylene copolymers by acompatibilizing agent, wherein the compatibilizing agent comprises (i)an acyclic carbon-carbon double bond having a first carbon atom and asecond carbon atom, (ii) an electron withdrawing group directly bondedto the first carbon atom in the acyclic carbon-carbon double bond, and(iii) a second carbon-carbon multiple bond in conjugation with theacyclic carbon-carbon double bond, wherein the second carbon-carbonmultiple bond is linked to the acyclic carbon-carbon double bond throughthe second carbon atom.

In a third embodiment, the invention provides a heterophasic polyolefinpolymer composition obtained by the process comprising the steps of:

(a) providing a propylene polymer phase comprising propylene polymersselected from the group consisting of polypropylene homopolymers andcopolymers of propylene and up to 50 wt. % of one or more comonomersselected from the group consisting of ethylene and C₄-C₁₀ α-olefinmonomers and an ethylene polymer phase comprising ethylene polymersselected from the group consisting of ethylene homopolymers andcopolymers of ethylene and one or more C₃-C₁₀ α-olefin monomers providedthat the ethylene content of the ethylene polymer phase is at least 8wt. %,

(b) providing a compatibilizing agent, wherein the compatibilizing agentcomprises (i) an acyclic carbon-carbon double bond having a first carbonatom and a second carbon atom, (ii) an electron withdrawing groupdirectly bonded to the first carbon atom in the acyclic carbon-carbondouble bond, and (iii) a second carbon-carbon multiple bond inconjugation with the acyclic carbon-carbon double bond, wherein thesecond carbon-carbon multiple bond is linked to the acycliccarbon-carbon double bond through the second carbon atom; and

(c) mixing the propylene polymer phase, the ethylene polymer phase andthe compatibilizing agent in the presence of free carbon radicals,whereby propylene polymers are bonded to ethylene polymers by thecompatibilizing agent, and whereby the propylene polymer phase and theethylene polymer phase form a heterophasic composition.

In a fourth embodiment, the invention provides a method of making aheterophasic polyolefin polymer composition, the method comprising thesteps of:

(a) providing a propylene polymer phase comprising propylene polymersselected from the group consisting of polypropylene homopolymers andcopolymers of propylene and up to 50 wt. % of one or more comonomersselected from the group consisting of ethylene and C₄-C₁₀ α-olefinmonomers, and an ethylene polymer phase comprising ethylene polymersselected from the group consisting of ethylene homopolymers andcopolymers of ethylene and one or more C₃-C₁₀ α-olefin monomers providedthat the ethylene content of the ethylene polymer phase is at least 8wt. %,

(b) providing a compatibilizing agent, wherein the compatibilizing agentcomprises (i) an acyclic carbon-carbon double bond having a first carbonatom and a second carbon atom, (ii) an electron withdrawing groupdirectly bonded to the first carbon atom in the acyclic carbon-carbondouble bond, and (iii) a second carbon-carbon multiple bond inconjugation with the acyclic carbon-carbon double bond, wherein thesecond carbon-carbon multiple bond is linked to the acycliccarbon-carbon double bond through the second carbon atom; and

(c) mixing the propylene polymer phase, the ethylene polymer phase andthe compatibilizing agent, in the presence of free carbon radicals,whereby the compatibilizing agent reacts with propylene polymers andethylene polymers thereby bonding propylene polymers to ethylenepolymers, and whereby the propylene polymer phase and the ethylenepolymer phase form a heterophasic composition.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows gel permeation chromatography (GPC) curves for Samples 1Aand 1B and C.S. 1A and C.S. 1B from Example 1.

FIG. 2 shows GPC curves for C.S. 2A-2D from Example 2.

DETAILED DESCRIPTION OF THE INVENTION

The following definitions are provided to define several of the termsused throughout this application.

As used herein, the term “substituted alkyl groups” refers to univalentfunctional groups derived from substituted alkanes by removal of ahydrogen atom from a carbon atom of the alkane. In this definition, theterm “substituted alkanes” refers to compounds derived from acyclicunbranched and branched hydrocarbons in which (1) one or more of thehydrogen atoms of the hydrocarbon is replaced with a non-hydrogen atom(e.g., a halogen atom) or a non-alkyl functional group (e.g., a hydroxygroup, aryl group, or heteroaryl group) and/or (2) the carbon-carbonchain of the hydrocarbon is interrupted by an oxygen atom (as in anether), a nitrogen atom (as in an amine), or a sulfur atom (as in asulfide).

As used herein, the term “substituted cycloalkyl groups” refers tounivalent functional groups derived from substituted cycloalkanes byremoval of a hydrogen atom from a carbon atom of the cycloalkane. Inthis definition, the term “substituted cycloalkanes” refers to compoundsderived from saturated monocyclic and polycyclic hydrocarbons (with orwithout side chains) in which (1) one or more of the hydrogen atoms ofthe hydrocarbon is replaced with a non-hydrogen atom (e.g., a halogenatom) or a non-alkyl functional group (e.g., a hydroxy group, arylgroup, or heteroaryl group) and/or (2) the carbon-carbon chain of thehydrocarbon is interrupted by an oxygen atom, a nitrogen atom, or asulfur atom.

As used herein, the term “substituted aryl groups” refers to univalentfunctional groups derived from substituted arenes by removal of ahydrogen atom from a ring carbon atom. In this definition, the term“substituted arenes” refers to compounds derived from monocyclic andpolycyclic aromatic hydrocarbons in which one or more of the hydrogenatoms of the hydrocarbon is replaced with a non-hydrogen atom (e.g., ahalogen atom) or a non-alkyl functional group (e.g., a hydroxy group).

As used herein, the term “substituted heteroaryl groups” refers tounivalent functional groups derived from substituted heteroarenes byremoval of a hydrogen atom from a ring atom. In this definition, theterm “substituted heteroarenes” refers to compounds derived frommonocyclic and polycyclic aromatic hydrocarbons in which (1) one or moreof the hydrogen atoms of the hydrocarbon is replaced with a non-hydrogenatom (e.g., a halogen atom) or a non-alkyl functional group (e.g., ahydroxy group) and (2) at least one methine group (—C═) of thehydrocarbon is replaced by a trivalent heteroatom and/or at least onevinylidene group (—CH═CH—) of the hydrocarbon is replaced by a divalentheteroatom.

As used herein, the term “alkanediyl groups” refers to divalentfunctional groups derived from alkanes by removal of two hydrogen atomsfrom the alkane. These hydrogen atoms can be removed from the samecarbon atom on the alkane (as in ethane-1,1-diyl) or from differentcarbon atoms (as in ethane-1,2-diyl).

As used herein, the term “substituted alkanediyl groups” refers todivalent functional groups derived from substituted alkanes by removalof two hydrogen atoms from the alkane. These hydrogen atoms can beremoved from the same carbon atom on the substituted alkane (as in2-fluoroethane-1,1-diyl) or from different carbon atoms (as in1-fluoroethane-1,2-diyl). In this definition, the term “substitutedalkanes” has the same meaning as set forth above in the definition ofsubstituted alkyl groups.

As used herein, the term “cycloalkanediyl groups” refers to divalentfunctional groups derived from cycloalkanes by removal of two hydrogenatoms from the cycloalkane. These hydrogen atoms can be removed from thesame carbon atom on the cycloalkane or from different carbon atoms.

As used herein, the term “substituted cycloalkanediyl groups” refers todivalent functional groups derived from substituted cycloalkanes byremoval of two hydrogen atoms from the alkane. In this definition, theterm “substituted cycloalkanes” has the same meaning as set forth abovein the definition of substituted cycloalkyl groups.

As used herein, the term “arenediyl groups” refers to divalentfunctional groups derived from arenes (monocyclic and polycyclicaromatic hydrocarbons) by removal of two hydrogen atoms from ring carbonatoms.

As used herein, the term “substituted arenediyl groups” refers todivalent functional groups derived from substituted arenes by removal oftwo hydrogen atoms from ring carbon atoms. In this definition, the term“substituted arenes” refers to compounds derived from monocyclic andpolycyclic aromatic hydrocarbons in which one or more of the hydrogenatoms of the hydrocarbon is replaced with a non-hydrogen atom (e.g., ahalogen atom) or a non-alkyl functional group (e.g., a hydroxy group).

As used herein, the term “heteroarenediyl groups” refers to divalentfunctional groups derived from heteroarenes by removal of two hydrogenatoms from ring atoms. In this definition, the term “heteroarenes”refers to compounds derived from monocyclic and polycyclic aromatichydrocarbons in which at least one methine group (—C═) of thehydrocarbon is replaced by a trivalent heteroatom and/or at least onevinylidene group (—CH═CH—) of the hydrocarbon is replaced by a divalentheteroatom.

As used herein, the term “substituted heteroarenediyl groups” refers todivalent functional groups derived from substituted heteroarenes byremoval of two hydrogen atoms from ring atoms. In this definition, theterm “substituted heteroarenes” has the same meaning as set forth abovein the definition of substituted heteroaryl groups.

Unless otherwise indicated, conditions are 25° C., 1 atmosphere ofpressure and 50% relative humidity, concentrations are by weight, andmolecular weight is based on weight average molecular weight. The term“polymer” as used in the present application denotes a material having aweight average molecular weight (Mw) of at least 5,000. The term“copolymer” is used in its broad sense to include polymers containingtwo or more different monomer units, such as terpolymers, and unlessotherwise indicated, includes random, block, and statistical copolymers.The concentration of ethylene or propylene in a particular phase or inthe heterophasic composition is based on the weight of reacted ethyleneunits or propylene units relative to the total weight of polyolefinpolymer in the phase or heterophasic composition, respectively,excluding any fillers or other non-polyolefin additives. Theconcentration of each phase in the overall heterogeneous polymercomposition is based on the total weight of polyolefin polymers in theheterophasic composition, excluding any fillers or other non-polyolefinadditives or polymers.

The subject heterophasic polyolefin polymers that may be advantageouslymodified according to the present invention are characterized by atleast two distinct phases—a propylene polymer phase comprising propylenepolymers selected from polypropylene homopolymers and copolymers ofpropylene and up to 50 wt. % of ethylene and/or C₄-C₁₀ α-olefins and anethylene polymer phase comprising ethylene polymers selected fromethylene homopolymers and copolymers of ethylene and C₃-C₁₀ α-olefins.The ethylene content of the ethylene polymer phase is at least 8 wt. %.When the ethylene phase is a copolymer of ethylene and C₃-C₁₀ α-olefins,the ethylene content of the ethylene phase may range from 8 to 90 wt. %.In one embodiment of the invention, the ethylene content of the ethylenephase is at least 50 wt. %. Either the propylene polymer phase or theethylene polymer phase may form the continuous phase and the other willform the discrete or dispersed phase. For example, the ethylene polymerphase may be the discontinuous phase and the polypropylene polymer phasemay be the continuous phase. In one embodiment of the invention, thepropylene content of the propylene polymer phase is greater than thepropylene content of the ethylene polymer phase.

The relative concentrations of the propylene polymer phase and theethylene polymer phase may vary over a wide range. By way of example,the ethylene polymer phase may comprise from 5 to 80 wt. % of the totalof propylene polymers and ethylene polymers in the composition and thepropylene polymer phase may comprise from 20 to 95 wt. % of the total ofpropylene polymers and ethylene polymers in the composition.

In various embodiments of the invention, (i) the ethylene content mayrange from 5 to 75 wt. %, or even 5 to 60 wt. %, based on the totalpropylene polymer and ethylene polymer content in the heterophasiccomposition, (ii) the ethylene polymer phase may be anethylene-propylene or ethylene-octene elastomer, and/or (iii) thepropylene content of the propylene polymer phase may be 80 wt. % orgreater.

The present invention is particularly useful to modify a polypropyleneimpact copolymer. The impact copolymer may be characterized by acontinuous phase comprising polypropylene polymers selected frompolypropylene homopolymers and copolymers of propylene and up to 50 wt.% of ethylene and/or C₄-C₁₀ α-olefins and a discontinuous phasecomprising elastomeric ethylene polymers selected from ethylene/C₃-C₁₀α-olefin monomers and the ethylene polymers have an ethylene content offrom 8 to 90 wt. %.

In various embodiments of the invention directed to propylene impactcopolymers, (i) the ethylene content of the discontinuous phase may befrom 8 to 80 wt. %, (ii) the ethylene content of the heterophasiccomposition may be from 5 to 30 wt. %, based on the total propylenepolymers and ethylene polymers in the composition; (iii) the propylenecontent of the continuous phase may be 80 wt. % or greater and/or (iv)the discontinuous phase may be from 5 to 35 wt. % of the total propylenepolymers and ethylene polymers in the composition.

Examples of heterophasic polyolefin polymers that may be modified areimpact copolymers characterized by a relatively rigid, polypropylenehomopolymer matrix (continuous phase) and a finely dispersed phase ofethylene-propylene rubber (EPR) particles. Polypropylene impactcopolymer may be made in a two-stage process, where the polypropylenehomopolymer is polymerized first and the ethylene-propylene rubber ispolymerized in a second stage. Alternatively, the impact copolymer maybe made in a three or more stages, as is known in the art. Suitableprocesses may be found in the following references: U.S. Pat. No.5,639,822 and U.S. Pat. No. 7,649,052 B2. Examples of suitable processesto make polypropylene impact copolymers are Spheripol®, Unipol®, Mitsuiprocess, Novolen process, Spherizone®, Catalloy®, Chisso process,Innovene®, Borstar®, and Sinopec process. These processes could useheterogeneous or homogeneous Ziegler-Natta or metallocene catalysts toaccomplish the polymerization.

Heterophasic polyolefin polymer composition may be formed by melt mixingtwo or more polymer compositions, which form at least two distinctphases in the solid state. By way of example, the heterophasicpolyolefin composition may comprise three distinct phases. Theheterophasic polyolefin polymer composition may result from melt mixingtwo or more types of recycled polyolefin compositions. Accordingly, thephrase “providing a heterophasic polyolefin polymer composition” as usedherein includes employing a polyolefin polymer composition in theprocess that is already heterophasic, as well as melt mixing two or morepolyolefin polymer compositions during the process, wherein the two ormore polyolefin polymer compositions form a heterophasic system. Forexample, the heterophasic polyolefin polymer may be made by melt mixinga polypropylene homopolymer and an ethylene/α-olefin copolymer, such asan ethylene/butene elastomer. Examples of suitable copolymers would beEngage™, Exact®, Vistamaxx®, Versify™, INFUSE™ Nordel™, Vistalon®,Exxelor™, and Affinity™. Furthermore, it can be understood that themiscibility of the polyolefin polymer components that form theheterophasic system may vary when the composition is heated above themelting point of the continuous phase in the system, yet the system willform two or more phases when it cools and solidifies. Examples ofheterophasic polyolefin polymer compositions may be found in U.S. Pat.No. 8,207,272 B2 and EP 1 391 482 B1.

In one embodiment of the invention, the heterophasic polyolefin polymerto be modified does not have any polyolefin constituents withunsaturated bonds, in particular, both the propylene polymers in thepropylene phase and the ethylene polymers in the ethylene phase are freeof unsaturated bonds.

In another embodiment of the invention, in addition to the propylenepolymer and ethylene polymer components, the heterophasic system mayinclude an elastomer, such as elastomeric ethylene copolymers,elastomeric propylene copolymers, styrene block copolymers, such asstyrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene(SEBS), styrene-ethylene-propylene-styrene (SEPS) andstyrene-isoprene-styrene (SIS), plastomers, ethylene-propylene-dieneterpolymers, LLDPE, LDPE, VLDPE, polybutadiene, polyisoprene, naturalrubber, and amorphous polyolefins. The rubbers may be virgin orrecycled.

The heterophasic polyolefin polymer composition is modified by mixingthe polymer composition with a compatibilizing agent in the presence offree radicals, which have been generated in the composition.

In one embodiment of the invention, the heterophasic polyolefin polymercomposition is modified by melt mixing the polymer composition with acompatibilizing agent in the presence of free radicals, which have beengenerated in the composition. The melt mixing step is conducted underconditions such that the composition is heated to above the meltingtemperature of the major polyolefin component of the composition andmixed while in the molten state. Examples of suitable melt mixingprocesses include melt compounding, such as in an extruder, injectionmolding, and mixing in a Banbury mixer or kneader. By way of example,the mixture may be melt mixed at a temperature of from 160° C. to 300°C. In particular, propylene impact copolymers may be melt mixed at atemperature of from 180° C. to 290° C. The polymer composition(propylene polymer phase and ethylene polymer phase), compatibilizingagent and an organic peroxide may be melt compounded in an extruder, ata temperature above the melting temperature of all of the polyolefinpolymers in the composition.

In another embodiment of the invention, the polymer may be dissolved ina solvent and the compatibilizing agent added to the polymer solution,and the radicals generated in solution. In another embodiment of theinvention, the compatibilizing agent may be combined with the polymer inthe solids state and free radicals could be generated during solid-stateshear pulverization as described in Macromolecules, “EsterFunctionalization of Polypropylene via Controlled Decomposition ofBenzoyl Peroxide during Solid-State Shear Pulverization”—vol. 46, pp.7834-7844 (2013).

Conventional processing equipment may be used to mix the propylenepolymers, ethylene polymers and compatibilizing agent together in asingle step, in the presence of free radicals that are either added tothe mixture, such as an organic peroxide, or generated in-situ, such asby shear, UV light, etc. Nevertheless, it is also possible to mixvarious combinations of the components in multiple steps and in varioussequences, and subsequently subject the mixture to conditions wherebythe compatibilizing agent reacts with the polyolefin polymers, asdescribed herein.

For example, the compatibilizing agent and/or the free radical generator(when a chemical compound is used) can be added to the polymer in theform of one or masterbatch compositions. Suitable masterbatchcompositions can comprise the compatibilizing agent and/or the freeradical generator in a carrier resin. The compatibilizing agent and/orthe free radical generator can be present in the masterbatch compositionin an amount of about 1 wt. % to about 80 wt. % based on the totalweight of the composition. Any suitable carrier resin can be used in themasterbatch compositions, such as any suitable thermoplastic polymer.For example, the carrier resin for the masterbatch compositions can be apolyolefin polymer, such as a polypropylene impact copolymer, apolyethylene homopolymer, a linear low density polyethylene polymer, apolyolefin wax, or mixtures of such polymers. The carrier resin can alsobe a propylene polymer or an ethylene polymer that is the same as orsimilar to the proplylene polymer or ethylene polymer present in theheterophasic polyolefin polymer composition. Such a masterbatchcomposition would allow the end user to manipulate the ratio ofpropylene polymer(s) to ethylene polymer(s) present in the heterophasicpolyolefin polymer composition. This may be preferred when the end userneeds to modify the propylene to ethylene ratio of a commercial resingrade in order to achieve the desired set of properties (e.g., balanceof impact and stiffness).

The compatibilizing agent comprises (i) an acyclic carbon-carbon doublebond having a first carbon atom and a second carbon atom, (ii) anelectron withdrawing group directly bonded to the first carbon atom inthe acyclic carbon-carbon double bond, and (iii) a second carbon-carbonmultiple bond in conjugation with the acyclic carbon-carbon double bond,wherein the second carbon-carbon multiple bond is linked to the acycliccarbon-carbon double bond through the second carbon atom. As utilized indescribing the compatibilizing agent, the term “acyclic carbon-carbondouble bond” refers to a carbon-carbon double bond that is not containedwithin a cyclic system, such as an aromatic ring. Thus, for example, thecarbon-carbon double bonds in the vinylidene groups (—CH═CH—) containedwithin a phenyl ring are not acyclic carbon-carbon double bonds.However, the carbon-carbon double bond contained within the vinyl groupof the compound styrene (i.e., phenylethene) is an acyclic carbon-carbondouble bond. Further, carbon-carbon double bonds that are pendant to acyclic system (e.g., the carbon-carbon bond is formed between a firstcarbon atom that is part of a cyclic system and a second carbon atomthat is not part of a cyclic system) are also acyclic carbon-carbondouble bonds.

The compatibilizing agent further comprises an electron withdrawinggroup directly bonded to one of the carbon atoms in the acycliccarbon-carbon double bond. The term “electron withdrawing group” is usedhere in its usual sense and refers to functional groups that drawelectron density away from the acyclic carbon-carbon double bond.Examples of suitable electron withdrawing groups include, but are notlimited to, halogens, cyano groups, nitro groups, carbonyl groups (suchas those contained in, for example, esters and amides), perfluorinatedalkyl groups, quaternary ammonium groups, and phosphoryl groups (such asthose contained in, for example, phosphine oxides, phosphonates, andphosphinates). In a preferred embodiment, the electron withdrawing groupis selected from the group consisting of cyano groups, nitro groups, andcarbonyl groups.

The compatibilizing agent further comprises a second carbon-carbonmultiple bond (i.e., another carbon-carbon multiple bond in addition tothe acyclic carbon-carbon double bond). This second carbon-carbonmultiple bond is in conjugation with the acyclic carbon-carbon doublebond and is linked to the acyclic carbon-carbon double bond through thesecond carbon atom of the acyclic double bond (i.e., the carbon atom towhich the electron withdrawing group is not attached). The secondcarbon-carbon multiple bond can be contained in either an acyclic orcyclic system. In a preferred embodiment, the second carbon-carbon is adouble bond that is contained in an aromatic or heteroaromatic system,such as within the aromatic/heteroaromatic ring or in a substituent(e.g., a vinyl group) attached to the aromatic/heteroaromatic ring. In apreferred embodiment, the second carbon-carbon multiple bond does nothave two or more electron donating groups attached to or in conjugationwith the second carbon-carbon multiple bond. The term “electron donatinggroup” is used here in its usual sense and refers to functional groupsthat donate electron density to the second carbon-carbon multiple bond.

In one preferred embodiment, the compatibilizing agent is selected fromthe group consisting of compounds conforming to the structure of Formula(I)

In the structure of Formula (I), R₁ is selected from the groupconsisting of aryl groups, substituted aryl groups, heteroaryl groups,substituted heteroaryl groups, and groups conforming to the structure ofFormula (V)

In the structure of Formula (V), R₅ and R₆ are independently selectedfrom the group consisting of hydrogen, alkyl groups, substituted alkylgroups, cycloalkyl groups, substituted cycloalkyl groups, aryl groups,substituted aryl groups, heteroaryl groups, and substituted heteroarylgroups or R₅ and R₆ can be combined to form a cyclic structure. Thevariable x is an integer selected from the group consisting of 0, 1, and2. In a preferred embodiment, the variable x is 0, R₅ is hydrogen, andR₆ is selected from the group consisting of aryl groups (e.g., C₆-C₁₂aryl groups), substituted aryl groups (e.g., C₆-C₁₂ substituted arylgroups), heteroaryl groups (e.g., C₄-C₁₂ heteroaryl groups), andsubstituted heteroaryl groups (e.g., C₄-C₁₂ substituted heteroarylgroups).

In the structure of Formula (I), R₂ is selected from the groupconsisting of hydrogen, halogens, alkyl groups, substituted alkylgroups, aryl groups, substituted aryl groups, heteroaryl groups, andsubstituted heteroaryl groups. If R₁ and R₂ are both aromatic groups,then (i) R₁ and R₂ are bridged by a direct bond, an alkanediyl group(e.g. a methanediyl group), an oxygen atom, a sulfur atom, or a nitrogenatom (e.g., a —N(H)— group), or (ii) at least one of R₁ and R₂ isselected from the group consisting of substituted aryl groupssubstituted with an electron withdrawing group, heteroaryl groups, andsubstituted heteroaryl groups.

In a preferred embodiment of the structure of Formula (I), at least oneof R₁ and R₂ is a group conforming to the structure of Formula (C),(CX), or (CXV)

In the structure of Formula (C), R₁₀₀ is selected from the groupconsisting of C(H), C(R₁₀₁), and a nitrogen atom. The variable a is aninteger from 0 to 4. Each R₁₀₁ is independently selected from the groupconsisting alkyl groups (e.g., C₁-C₁₀ alkyl groups), substituted alkylgroups (e.g., C₁-C₁₀ substituted alkyl groups), aryl groups (e.g.,C₆-C₁₂ aryl groups), substituted aryl groups (e.g., C₆-C₁₂ substitutedaryl groups), heteroaryl groups (e.g., C₄-C₁₂ heteroaryl groups),substituted heteroaryl groups (e.g., C₄-C₁₂ substituted heteroarylgroups), halogens, nitro groups, cyano groups, amine groups, hydroxygroups, alkoxy groups (e.g., C₁-C₁₀ alkoxy groups), aryloxy groups(e.g., C₆-C₁₂ aryloxy groups), alkenyl groups (e.g., C₂-C₁₀ alkenylgroups), alkynyl groups (e.g., C₂-C₁₀ alkynyl groups), alkyl estergroups (e.g., C₁-C₁₀ alkyl ester groups), and aryl ester groups (e.g.,C₆-C₁₂ aryl ester groups). Further, two adjacent R₁₀₁ groups can belinked to form a fused ring structure, such as a polycyclic aryl group.In the structure of Formula (CX), R₁₁₀ is selected from the groupconsisting of an oxygen atom, a sulfur atom, and N(R₁₁₅). R₁₁₅ isselected from the group consisting of hydrogen, alkyl groups (e.g.,C₁-C₁₀ alkyl groups), substituted alkyl groups (e.g., C₁-C₁₀ substitutedalkyl groups), aryl groups (e.g., C₆-C₁₂ aryl groups), and substitutedaryl groups (e.g., C₆-C₁₂ substituted aryl groups). R₁₁₁ is selectedfrom the group consisting of C(H), C(R₁₁₂), and a nitrogen atom. R₁₁₂ isselected from the group consisting of alkyl groups (e.g., C₁-C₁₀ alkylgroups), substituted alkyl groups (e.g., C₁-C₁₀ substituted alkylgroups), aryl groups (e.g., C₆-C₁₂ aryl groups), substituted aryl groups(e.g., C₆-C₁₂ substituted aryl groups), heteroaryl groups (e.g., C₄-C₁₂heteroaryl groups), substituted heteroaryl groups (e.g., C₄-C₁₂substituted heteroaryl groups), halogens, nitro groups, cyano groups,amine groups, hydroxy groups, alkoxy groups (e.g., C₁-C₁₀ alkoxygroups), aryloxy groups (e.g., C₆-C₁₂ aryloxy groups), alkenyl groups(e.g., C₁-C₁₀ alkenyl groups), alkynyl groups (e.g., C₂-C₁₀ alkynylgroups), alkyl ester groups (e.g., C₂-C₁₀ alkyl ester groups), and arylester groups (e.g., C₆-C₁₂ aryl ester groups). Further, two adjacentR₁₁₂ groups can be linked to form a fused ring structure, such as apolycyclic aryl group. The variable b is an integer from 0 to 2. In thestructure of Formula (CXV), R₁₁₀ and R₁₁₂ are selected from the samegroups described above for Formula (CX), and the variable c is aninteger from 0 to 3.

In the structure of Formula (I), R₃ and R₄ are independently selectedfrom the group consisting of hydrogen, alkyl groups, substituted alkylgroups, cycloalkyl groups, substituted cycloalkyl groups, cyano groups,nitro groups, and groups conforming to a structure of Formula (VI),(VII), (VIII), or (IX)

In the structures of Formulae (VI), (VII), (VIII), and (IX), R₇ and R₉are independently selected from the group consisting of alkyl groups(e.g., C₁-C₂₂ alkyl groups), substituted alkyl groups (e.g., C₁-C₂₂substituted alkyl groups), cycloalkyl groups (e.g., C₃-C₂₂ cycloalkylgroups), substituted cycloalkyl groups (e.g., C₃-C₂₂ substitutedcycloalkyl groups), aryl groups (e.g., C₆-C₂₂ aryl groups), substitutedaryl groups (e.g., C₆-C₂₂ substituted aryl groups), heteroaryl groups(e.g., C₄-C₂₂ heteroaryl groups), and substituted heteroaryl groups(e.g., C₄-C₂₂ substituted heteroaryl groups). R₈ is selected from thegroup consisting of hydrogen, alkyl groups (e.g., C₁-C₂₂ alkyl groups),substituted alkyl groups (e.g., C₁-C₂₂ substituted alkyl groups),cycloalkyl groups (e.g., C₃-C₂₂ cycloalkyl groups), substitutedcycloalkyl groups (e.g., C₃-C₂₂ substituted cycloalkyl groups), arylgroups (e.g., C₆-C₂₂ aryl groups), substituted aryl groups (e.g., C₆-C₂₂substituted aryl groups), heteroaryl groups (e.g., C₄-C₂₂ heteroarylgroups), and substituted heteroaryl groups (e.g., C₄-C₂₂ substitutedheteroaryl groups). For groups conforming to the structure of Formula(VIII), R₇ and R₉ can be combined to form a cyclic structure. Lastly, inthe structure of Formula (I), at least one of R₃ and R₄ is selected fromthe group consisting of cyano groups, nitro groups, and groupsconforming to a structure of Formula (VI), (VII), (VIII), or (IX). In apreferred embodiment, R₃ and R₄ are independently selected from thegroup consisting of hydrogen, cyano groups, nitro groups, and groupsconforming to the structure of Formula (VI), where R₇ is an alkyl group(e.g., a C₁-C₂₂ alkyl group).

In another preferred embodiment, the compatibilizing agent is selectedfrom the group consisting of compounds conforming to the structure ofFormula (X)

In the structure of Formula (X), R₁₀ is selected from the groupconsisting of arenediyl groups, substituted arenediyl groups,heteroarenediyl groups, substituted heteroarenediyl groups, and groupsconforming to the structure of Formula (XV)

In the structure of Formula (XV), R₁₅ is selected from the groupconsisting of a direct bond between R₁₆ and R₁₇, an oxygen atom, analkanediyl group, and a substituted alkanediyl group. R₁₆ and R₁₇ areindependently selected from the group consisting of arenediyl groups,substituted arenediyl groups, heteroarenediyl groups, and substitutedheteroarenediyl groups. In a preferred embodiment, R₁₀ is a groupconforming to a structure selected from the group consisting of Formulae(CXX) (CXXV), (CXXX), and (CXXXV)

In the structures of Formulae (CXXX) and (CXXXV), R₁₄₀ is selected fromthe group consisting of an oxygen atom, a sulfur atom, —N(H)—, and—N(R₁₄₅)—, where R₁₄₅ is selected from the group consisting of C₁-C₁₀alkyl groups and C₆-C₁₂ aryl groups. In the structures of Formulae(CXX), (CXXV), (CXXX), and (CXXXV), each R₁₄₁ is selected from the groupconsisting of halogen atoms. The variable d is an integer from 0 to 2,and the variable e is an integer from 0 to 4. In another preferredembodiment, R₁₀ is a group conforming to the structure of Formula (XV)in which R₁₅ is selected from a direct bond and an oxygen atom and R₁₆and R₁₇ are groups conforming to the structure of Formula (CXX).

In the structure of Formula (X), R₁₁, R₁₂, R₁₃, and R₁₄ areindependently selected from the group consisting of hydrogen, alkylgroups, substituted alkyl groups, cycloalkyl groups, substitutedcycloalkyl groups, cyano groups, nitro groups, and groups conforming toa structure of Formula (VI), (VII), (VIII), or (IX) as described above.In the structure of Formula (X), at least one of R₁₁ and R₁₂ and atleast one of R₁₃ and R₁₄ is selected from the group consisting of cyanogroups, nitro groups, and groups conforming to a structure of Formula(VI), (VII), (VIII), or (IX).

In another preferred embodiment, the compatibilizing agent is selectedfrom the group consisting of compounds conforming to the structure ofFormula (XX)

In the structure of Formula (XX), R₂₀ is a divalent linking group. Thedivalent linking group can be any suitable divalent linking group.Suitable divalent linking groups include, but are not limited to,alkanediyl groups, substituted alkanediyl groups, cycloalkanediylgroups, substituted cycloalkanediyl groups, arenediyl groups,substituted arenediyl groups, heteroarenediyl groups, and substitutedheteroarenediyl groups. In one preferred embodiment, R₂₀ is a groupconforming to the structure of Formula (XXV)

In the structure of Formula (XXV), R₂₇ is selected from the groupconsisting of an oxygen atom, —N(H)—, and —N(R₂₉)—, where R₂₉ isselected from the group consisting of alkyl groups, substituted alkylgroups, cycloallkyl groups, and substituted cycloalkyl groups. R₂₈ isselected from the group consisting of alkanediyl groups andcycloalkanediyl groups. In a preferred embodiment, R₂₇ are oxygen atomsand R₂₈ is an alkandiyl group (e.g., a C₁-C₈ alkanediyl group). Inanother preferred embodiment, R₂₀ is a group conforming to the structureof Formula (XXX)

In the structure of Formula (XXX), R₃₀ is selected from the groupconsisting of alkanediyl groups and cycloalkanediyl groups. R₃₁ isselected from the group consisting of an oxygen atom, —N(H)—, and—N(R₂₉)—, where R₂₉ is selected from the group consisting of alkylgroups, substituted alkyl groups, cycloallkyl groups, and substitutedcycloalkyl groups. R₃₂ is selected from the group consisting ofarenediyl groups, substituted arenediyl groups, heteroarenediyl groups,substituted heteroarenediyl groups, and —R₃₅R₃₆—, where R₃₅ is selectedfrom the group consisting of arenediyl groups, substituted arenediylgroups, heteroarenediyl groups, and substituted heteroarenediyl groups,and R₃₆ is selected from the group consisting of alkanediyl groups(e.g., C₁-C₄ alkanediyl groups). In a preferred embodiment, R₃₀ is analkanediyl group (e.g., a C₁-C₈ alkanediyl group), R₃₁ are oxygen atoms,and R₃₂ are selected from heteroareneidyl groups, substitutedheteroarenediyl groups, and —R₃₅R₃₆—. More specifically, in such apreferred embodiment, R₃₂ preferably conforms to the structure ofFormula (XL)

In the structure of Formula (XX), R₂₁ and R₂₂ are selected from thegroup consisting of cyano groups, nitro groups, and groups conforming toa structure of Formula (VI), (VII), (VIII), or (IX) as described above.R₂₃, R₂₄, R₂₅, and R₂₆ are independently selected from the groupconsisting of hydrogen, alkyl groups, substituted alkyl groups,cycloalkyl groups, substituted cycloalkyl groups, aryl groups,substituted aryl groups, heteroaryl groups, substituted heteroarylgroups, and groups conforming to the structure of Formula (V) asdescribed above. In the structure of Formula (XX), at least one of R₂₃and R₂₄ and at least one of R₂₅ and R₂₆ is selected from the groupconsisting of aryl groups, substituted aryl groups, heteroaryl groups,substituted heteroaryl groups, and groups conforming to the structure ofFormula (V). Further, if R₂₃ and R₂₄ are both aromatic groups, then (i)R₂₃ and R₂₄ are bridged by a direct bond or an alkyl group or (ii) atleast one of R₂₃ and R₂₄ is selected from the group consisting ofsubstituted aryl groups substituted with an electron withdrawing group,heteroaryl groups, and substituted heteroaryl groups. And, if R₂₅ andR₂₆ are both aromatic groups, then (i) R₂₅ and R₂₆ are bridged by adirect bond or an alkyl group or (ii) at least one of R₂₅ and R₂₆ isselected from the group consisting of substituted aryl groupssubstituted with an electron withdrawing group, heteroaryl groups, andsubstituted heteroaryl groups.

The concentration of the compatibilizing agent in the composition can bevaried to meet the objectives of the end user. For example, theconcentration can be varied in order to achieve a desired increase inthe MFR of the polymer composition with a minimal decrease (orpotentially even an increase) in the strength of the polymer, inparticular the impact strength. In a preferred embodiment, thecompatibilizing agent can be present in an amount of about 10 ppm ormore, about 50 ppm or more, about 100 ppm or more, about 150 ppm ormore, or about 200 ppm or more, based on the total weight of the polymercomposition. In another preferred embodiment, the compatibilizing agentcan be present in an amount of about 5 wt. % (50,000 ppm) or less, about4 wt. % (40,000 ppm) or less, about 3 wt. % (30,000 ppm) or less, about2 wt. % (20,000 ppm) or less, about 1 wt. % (10,000 ppm) or less, orabout 0.5 wt. % (5,000 ppm) or less, based on the total weight of thepolymer composition. Thus, in certain preferred embodiments, thecompatibilizing agent can be present in an amount of about 10 to about50,000 ppm, about 100 to about 10,000 ppm, or about 200 to about 5,000ppm, based on the total weight of the polymer composition.

When a chemical free radical generator is employed (as discussed below),the concentration of the compatibilizing agent in the polymercomposition can additionally or alternatively be expressed in terms of aratio between the amount of the compatibilizing agent and the amount ofthe chemical free radical generator. In order to normalize this ratiofor differences in the molecular weight of compatibilizing agents andnumber of peroxide bonds in the chemical free radical generators, theratio is usual expressed as a ratio of the number of moles ofcompatibilizing agent present in the composition to the molarequivalents of peroxide bonds (O—O bonds) present from the addition ofthe chemical free radical generator. Preferably, the ratio (i.e., ratioof moles of compatibilizing agent to molar equivalents of peroxidebonds) is about 1:10 or more, about 1:5 or more, about 3:10 or more,about 2:5 or more, about 1:2 or more, about 3:5 or more, about 7:10 ormore, about 4:5 or more, about 9:10 or more, or about 1:1 or more. Inanother preferred embodiment, the ratio is about 10:1 or less, about 5:1or less, about 10:3 or less, about 5:2 or less, about 2:1 or less, about5:3 or less, about 10:7 or less, about 5:4 or less, about 10:9 or less,or about 1:1 or less. Thus, in a series of preferred embodiments, thecompatibilizing agent can be present in the composition in a ratio ofmoles of compatibilizing agent to molar equivalents of peroxide bonds ofabout 1:10 to about 10:1, about 1:5 to about 5:1, about 1:4 to about4:1, about 3:10 to about 10:3, about 2:5 to about 5:2, or about 1:2 toabout 2:1.

A free radical generator is employed in the present invention to causepolymer chain scission and thereby positively affect the MFR of theheterophasic polyolefin polymer composition, while generating sufficientfree radicals to foster the reaction of the compatibilizing agent withthe polyolefin polymers in the composition. The free radical generatormay be a chemical compound, such as an organic peroxide or a bis-azocompound, or free radicals may be generated by applying ultrasound,shear, an electron beam (for example β-rays), light (for example UVlight), heat and radiation (for example γ-rays and X-rays), to thereaction system, or combinations of the foregoing.

Organic peroxides having one or more 0-0 functionalities are ofparticular utility in the present invention. Examples of such organicperoxides include: 2,5-dimethyl-2,5-di(t-butylperoxy)hexane,2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3,3,6,6,9,9-pentamethyl-3-(ethyl acetate)-1,2,4,5-tetraoxycyclononane, t-butyl hydroperoxide, hydrogen peroxide, dicumyl peroxide,t-butyl peroxy isopropyl carbonate, di-t-butyl peroxide, p-chlorobenzoylperoxide, dibenzoyl diperoxide, t-butyl cumyl peroxide; t-butylhydroxyethyl peroxide, di-t-amyl peroxide and2,5-dimethylhexene-2,5-diperisononanoate, acetylcyclohexanesulphonylperoxide, diisopropyl peroxydicarbonate, tert-amyl perneodecanoate,tert-butyl-perneodecanoate, tert-butylperpivalate, tert-amylperpivalate,bis(2,4-dichlorobenzoyl)peroxide, diisononanoyl peroxide, didecanoylperoxide, dioctanoyl peroxide, dilauroyl peroxide,bis(2-methylbenzoyl)peroxide, disuccinoyl peroxide, diacetyl peroxide,dibenzoyl peroxide, tert-butyl per-2-ethylhexanoate,bis(4-chlorobenzoyl)peroxide, tert-butyl perisobutyrate, tert-butylpermaleate, 1,1-bis(tert-butylperoxy)-3,5,5-trimethylcyclo-hexane,1,1-bis(tert-butylperoxy)cyclohexane, tert-butyl peroxyisopropylcarbonate, tert-butyl perisononaoate, 2,5-dimethylhexane 2,5-dibenzoate,tert-butyl peracetate, tert-amyl perbenzoate, tert-butyl perbenzoate,2,2-bis(tert-butylperoxy)butane, 2,2-bis(tert-butylperoxy)propane,dicumyl peroxide, 2,5-dimethylhexane 2,5-di-tert-butylperoxid,3-tert-butylperoxy-3-phenyl phthalide, di-tert-amyl peroxide,α,α′-bis(tert-butylperoxyisopropyl)benzene,3,5-bis(tert-butylperoxy)-3,5-dimethyl-1,2-dioxolane, di-tert-butylperoxide, 2,5-dimethylhexyne 2,5-di-tert-butyl peroxide,3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxacyclononane, p-menthanehydroperoxide, pinane hydroperoxide, diisopropylbenzenemono-α-hydroperoxide, cumene hydroperoxide or tert-butyl hydroperoxide.

The organic peroxide can be present in the polymer composition in anysuitable amount. The suitable amount of organic peroxide will dependupon several factors, such as the particular polymer that is used in thecomposition, the starting MFR of the polymer, and the desired change inthe MFR of the polymer. In a preferred embodiment, the organic peroxidecan be present in the polymer composition in an amount of about 10 ppmor more, about 50 ppm or more, or about 100 ppm or more, based on thetotal weight of the polymer composition. In another preferredembodiment, the organic peroxide can be present in the polymercomposition in an amount of about 2 wt. % (20,000 ppm) or less, about 1wt. % (10,000 ppm) or less, about 0.5 wt. % (5,000 ppm) or less, about0.4 wt. % (4,000 ppm) or less, about 0.3 wt. % (3,000 ppm) or less,about 0.2 wt. % (2,000 ppm) or less, or about 0.1 wt. % (1,000 ppm) orless, based on the total weight of the polymer composition. Thus, in aseries of preferred embodiments, the organic peroxide can be present inthe polymer composition in an amount of about 10 to about 20,000 ppm,about 50 to about 5,000 ppm, about 100 to about 2,000 ppm, or about 100to about 1,000 ppm, based on the total weight of the polymercomposition. The amount of organic peroxide can also be expressed interms of a molar ratio of the compatibilizing agent and peroxide bonds,as is described above.

Suitable bis azo compounds may also be employed as a source of freeradicals. Such azo compounds are for example2,2′-azobisisobutyronitrile, 2,2′-azobis(2-methylbutyronitrile),2,2′-azobis(2,4-dimethylvaleronitrile),2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile),1,1′-azobis(1-cyclohexanecarbonitrile),2,2′-azobis(isobutyramide)dihydrate,2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, dimethyl2,2′-azobisisobutyrate, 2-(carbamoylazo)isobutyronitrile,2,2′-azobis(2,4,4-trimethylpentane), 2,2′-azobis(2-methyl-propane),2,2′-azobis(N,N′-dimethyleneisobutyramidine) as free base orhydrochloride, 2,2′-azobis(2-amidinopropane) as free base orhydrochloride,2,2′-azobis{2-methyl-N-[1,1-bis(hydroxymethyl)ethyl]propionamide} or2,2′-azobis{2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide}.

Other chemical compounds useful as free radical initiators include2,3-dimethyl-2,3-diphenylbutane and sterically hindered hydroxylamineester.

The various radical generators may be employed alone or in combination.

The heterophasic polyolefin composition of the present invention iscompatible with various types additives, conventionally used inthermoplastic compositions, including stabilizers, UV absorbers,hindered-amine light stabilizers (HALS), antioxidants, flame retardants,acid neutralizers, slip agents, antiblocking agents, antistatic agents,antiscratch agents, processing aids, blowing agents, colorants,opacifiers, clarifiers, and/or nucleating agents. By way of furtherexample, the composition may comprise fillers, such as calciumcarbonate, talc, glass fibers, glass spheres, inorganic whiskers such asHyperform® HPR-803i available from Milliken Chemical, USA, magnesiumoxysulfate whiskers, calcium sulfate whiskers, calcium carbonatewhiskers, mica, wollastonite, clays, such as montmorillonite, andbio-sourced or natural filler. The additives may comprise up to 75 wt. %of the total components in the modified heterophasic polyolefincomposition.

The heterophasic polyolefin composition of the present invention may beused in conventional polymer processing applications, including but notlimited to injection molding, thin-wall injection molding, single-screwcompounding, twin-screw compounding, Banbury mixing, co-kneader mixing,two-roll milling, sheet extrusion, fiber extrusion, film extrusion, pipeextrusion, profile extrusion, extrusion coating, extrusion blow molding,injection blow molding, injection stretch blow molding, compressionmolding, extrusion compression molding, compression blow forming,compression stretch blow forming, thermoforming, and rotomolding.Thermoplastic polymer articles made using the thermoplastic polymercomposition of the invention can be comprised of multiple layers, withone or any suitable number of the multiple layers containing athermoplastic polymer composition of the invention. By way of example,typical end-use products include containers, packaging, automotiveparts, bottles, expanded or foamed articles, appliance parts, closures,cups, furniture, housewares, battery cases, crates, pallets, films,sheet, fibers, pipe, and rotationally molded parts.

The following examples further illustrate the subject matter describedabove but, of course, should not be construed as in any way limiting thescope thereof. The following methods, unless noted, were used todetermine the properties described in the following examples.

Each of the compositions was compounded by blending the components in aclosed container for approximately one minute. The compositions werethen melt compounded on a Prism TSE-16-TC co-rotating, fullyintermeshing, parallel, twin-screw extruder with a 16 mm screw diameterand a length/diameter ratio of 25:1. The barrel temperature of theextruder was ramped from approximately 195° C. to approximately 215° C.,and the screw speed was set at approximately 500 rpm. The extrudate (inthe form of a strand) for each polypropylene copolymer composition wascooled in a water bath and subsequently pelletized.

The pelletized compositions were then used to form bars by injectionmolding the compositions on a Nissei HM7 7 ton injection molder having a14 mm diameter screw. The barrel temperature of the injection molder wasapproximately 215 to 230° C., and the mold temperature was approximately25° C. The resulting bars measured approximately 80 mm long,approximately 10 mm wide, and approximately 4.0 mm thick.

The melt flow rate (MFR) was determined on the pelletized compositionsaccording to (ASTM D1238) at 230° C. with a load of 2.16 kg forpolypropylene.

The notched Izod impact strength for the bars was measured according toISO method 180/A. The notched Izod impact strength was measured at +23°C. on bars that had been conditioned at either +23° C. or −30° C.

The molecular weight distribution (MWD) as well as the weight average ofsaid distribution, M_(W), was determined using gel permeationchromatography (GPC), also referred to as size exclusion chromatography(SEC). All measurements were conducted by the use of the Agilent PL-GPC220 GPC/SEC system containing (3) 300×7.5 mm PLgel 10 μm Mixed-B LS, aRefractive Index detector, Viscometer and 15° and 90° Light Scatteringdetector (at 160° C.) with trichlorobenzene inhibited with 125 ppmbutylhydroxytoluene as mobile phase, a column temperature of 160° C. anda sample concentration of approx. 1 mg/ml. In the examples listed below,a 15° light scattering detector is chosen to measure concentration. Gelpermeation chromatography is a separation technique in which moleculesare separated on the basis of hydrodynamic molecular volume or size.With proper column calibration or by the use ofmolecular-weight-sensitive detectors, such as light scattering orviscometry the molecular weight distribution and the statisticalmolecular weight averages can be obtained. In gel permeationchromatography, molecules pass through a column via a combination oftransport into and through beads along with between beads in the column.The time required for passage of a molecule through the column isdecreased with increasing molecular weight. The amount of polymerexiting the column at any given time is measured with various detectors.A more in depth description of the instrumentation and detectors can befound in the chapter titled “Composition, Molar Mass and Molar MassDistribution” in Characterization and Analysis of Polymers by RonClavier (2008).

Xylene solubles were determined by a modified ASTM D5492-10 and are ameasure of the amount of rubber present in the heterophasicpolypropylene copolymers. Approximately 0.6 g of polymer was weighed outand placed into a round-bottom flask along with a stir bar. 50 mL ofxylene was added to the polymer in the flask. The polymer xylene mixturewas heated to reflux temperature while vigorously stirring. Once thereflux temperature was reached, the solution was stirred for anadditional 30 min then cooled to room temperature. The resultingpolymer/xylene mixture was gently stirred to break up any precipitatedpolymer gel then poured through a No. 4 filter paper, both the filtratecontaining the soluble fraction and the insoluble fraction werecollected. A 10 mL aliquot of the filtrate was taken with a Class Apipet and transferred into a weighed pan. The pan containing thefiltrate was then placed on a temperature-controlled hot platemaintaining a temperature of 155° C. to evaporate the xylene. Once mostof the xylene was evaporated, the pan was transferred to a vacuum ovenset at a temperature of 80±10° C. The pressure was reduced to less than13.3 kPa and the sample was dried for approximately 2 hours or until aconstant weight was achieved. The pan mass was then subtracted givingthe mass of the residual soluble polymer. The percentage of solublepolymer in the original sample was calculated as follows:S _(s)=((V _(bo) /v _(b1)*(W ₂ −W ₁))/W ₀)*100where: S_(s)=soluble fraction of sample, %; V_(bo)=original volume ofsolvent, mL; V_(b1)=volume of aliquot used for soluble determination,mL; W₂=mass of pan and soluble, g; W₁=mass of pan, g; and W_(o)=mass oforiginal sample, g.

EXAMPLE 1

The following example demonstrates the modification of a heterophasicpolyolefin composition and performance enhancements achieved, accordingto the method of the present invention.

Four heterophasic polymer compositions were produced. Comparative Sample1A (C.S. 1A) was an unmodified polypropylene copolymer. ComparativeSample 1B (C.S. 1B) was made with the same polypropylene copolymervis-broken using a peroxide. Samples 1A and 1B were made with the samevis-broken polypropylene copolymer compounded with2-(furan-2-ylmethylene)malononitrile (Compound ID 1 from Table 7 below)as a compatibilizing agent. The general formulation for these samples isset forth in Table 1.

TABLE 1 Heterophasic polypropylene copolymer formulations ComponentLoading Polypropylene copolymer Balance (LyondellBasell Pro-Fax SD375Swith approximately 19% xylene solubles) Primary antioxidant (Irganox ®1010) 500 ppm Secondary antioxidant (Irgafos ® 168) 1000 ppm  Acidscavenger (calcium stearate) 800 ppm Peroxide (Varox DBPH) See Table 2Additive (Compatibilizing Agent) See Table 2 Compound ID 1 Irganox ®1010 is available from BASF Irgafos ® 168 is available from BASF VaroxDBPH is an organic peroxide available from R.T. Vanderbilt Company

Each of the compositions listed in Table 2 was mixed, extruded, andinjection molded according to the above procedure. The bars were thensubjected to melt flow rate and Izod impact testing described above, andevaluated using the 15° light scattering detector signal during testingby Gel Permeation Chromatography (GPC).

TABLE 2 Performance in medium-impact, heterophasic polypropylenecopolymer. Sample C.S. 1A C.S. 1B 1A 1B Peroxide Loading (ppm) — 10001000  1000  Additive Loading (Molar — — 1:1 2:1 ratio Additive: O—O)Additive Loading (ppm) — — 992  1985  Melt Flow Rate (g/10 min) 17 10243 27 Izod impact at 23° C. (J/m) 111 54 156* Non-break Izod impact at−30° C. (J/m) 49 38 55 53 *also gave partial failures and non-breaks

The resulting change in polymer molecular weight for each of thecompositions is shown in FIG. 1. When peroxide is added topolypropylene, the molecular weight is decreased as indicated by thepeak shift to longer retention times and there is a relative decrease insignal at retention times less than about 1000 seconds. The inventivecompositions (Samples 1A and 1B) show a shift back to shorter retentiontimes (higher molecular weights) and a pronounced shoulder at aretention time of about 950 seconds, not observed in the unmodified orperoxide modified heterophasic resin. This shoulder indicates theformation of a modified polymer with molecular weight higher than thatof either the unmodified or peroxide modified heterophasic resin.

EXAMPLE 2

The following example investigates the effects of using acompatibilizing agent in a non-heterophasic polyolefin composition.

Four non-heterophasic polymer compositions were produced. ComparativeSample 2A (C.S. 2A) was an unmodified polypropylene polymer. ComparativeSample 2B (C.S. 2B) was made with the same polypropylene polymervis-broken using a peroxide. Comparative Samples 2C and 2D were madewith the same vis-broken polypropylene polymer compounded with2-(furan-2-ylmethylene)malononitrile as a compatibilizing agent. Thegeneral formulation for these samples is set forth in Table 3.

TABLE 3 Non-heterophasic polypropylene homopolymer formulationsComponent Loading Polypropylene Homopolymer Balance (TotalPetrochemicals 3276) Primary antioxidant (Irganox ® 1010) 500 ppmSecondary antioxidant (Irgafos ® 168) 1000 ppm  Acid scavenger (calciumstearate) 800 ppm Peroxide (Varox DBPH) See Table 4 Additive(Compatibilizing Agent) See Table 4 2-(furan-2-ylmethylene)malononitrileIrganox ® 1010 is available from BASF Irgafos ® 168 is available fromBASF Varox DBPH is an organic peroxide available from R. T. VanderbiltCompany

TABLE 4 Performance in non-heterophasic polypropylene homopolymerformulations. Sample C.S. 2A C.S. 2B C.S. 2C C.S. 2D Peroxide Loading(ppm) — 1000  1000 1000 Additive Loading (Molar — — 1:1 2:1 ratioAdditive: O—O) Additive Loading (ppm) — — 992 1985 Melt Flow Rate (g/10min) 2 34 18 9 Izod impact at 23° C. (J/m) 15 17 13 12

Each of the compositions listed in Table 4 was mixed, extruded, andinjection molded according to the above procedure. The bars were thensubjected to melt flow rate and Izod impact testing described above, andevaluated using the 15° light scattering detector signal during testingby Gel Permeation Chromatography (GPC).

The GPC data for Comparative Samples 2A-2D are shown in FIG. 2. Whenperoxide is added to the homopolymer polypropylene, the molecular weightis decreased, as indicated by the shift to longer retention times.Comparative Samples 2C and 2D, which contain2-(furan-2-ylmethylene)malononitrile, show a shift back to shorterretention times (higher molecular weights) as the additive counteractsthe peroxide. However, the samples do not show the shoulder as seen withSamples 1A and 1B in FIG. 1.

EXAMPLE 3

The following example demonstrates the production of severalheterophasic polyolefin compositions as described above and investigatesthe performance enhancements achieved through the incorporation of thecompatibilizing agents as described above.

In order to permit a comparison of the various compatibilizing agentsand their effects on the physical properties of a heterophasic polymercomposition, the relationship between melt flow rate and Izod impact ofa commercially-available polypropylene copolymer (LyondellBasell Pro-FaxSD375S) was investigated by vis-breaking the polymer using severaldifferent loadings of a commercially-available peroxide (Varox BDPH). Acompatibilizing agent according to the invention was not used in thesecompositions. The raw MFR and Izod impact values obtained from thesemeasurements were then indexed to the MFR and Izod impact values of thevirgin, unmodified polymer (not vis-broken) to provide relative values.The relative MFR and Izod impact values are reported in Table 5 below.

TABLE 5 Relative MFR and Izod impact values of a commercially- availablepolypropylene copolymer. Peroxide Loading (ppm) Relative MFR (M_(R))Relative Izod (I_(R)) 0 1.00 1.00 250 2.09 0.74 500 3.35 0.63 1000 5.440.54

These relative values were then plotted and a trendline fitted to theplot to produce a mathematical equation expressing the observedrelationship between the relative MFR and the relative Izod impact ofthe polymer. The fit of a trendline yielded the following mathematicalequation:I _(R)=0.9866×M _(R) ^(−0.369)In the equation, I_(R) is the relative Izod impact value and M_(R) isthe relative MFR. The R² value for the trendline was 0.996, indicatingthat the trendline fit the data very well. The quality of the fit alsoshows that the equation can be used to calculate an expected Izod impactvalue once the MFR has been measured and the relative MFR calculated. Inthis sense, the “expected Izod impact value” is the value that thevis-broken polymer is expected to exhibit at a given relative MFR in theabsence of a compatibilizing agent. When a compatibilizing agent isused, this expected Izod impact value can then be compared to themeasured Izod impact value to ascertain and quantify the effect of thecompatibilizing agent on the strength of the polymer. This differencebetween the expected Izod impact value and the measured Izod impactvalue is reported below in Tables 8 and 9 for several compounds.

Compatibilizing agents according to the invention and comparativecompounds were each melt mixed into different batches of heterophasicpolypropylene copolymer compositions, in accordance with the generalformulation set forth in Table 6. Tables 7-9 set forth the structure ofthe compatibilizing agent or comparative compound used in eachcomposition.

TABLE 6 Polypropylene copolymer formulations. Component LoadingPolypropylene copolymer Balance (LyondellBasell Pro-Fax SD375S withapproximately 19% xylene solubles) Primary antioxidant (Irganox ® 1010) 500 ppm Secondary antioxidant (Irgafos ® 168) 1000 ppm Acid scavenger(calcium stearate)  800 ppm Peroxide (Varox DBPH) 1000 ppmCompatibilizing Agent See Tables 7-9 Irganox ® 1010 is available fromBASF Irgafos ® 168 is available from BASF Varox DBPH is available fromR. T. Vanderbilt Company

Each of the heterophasic polypropylene copolymer compositions was mixed,extruded, and injection molded according to the procedure describedabove. The melt flow rate and Izod impact values (at 23° C.) for thecompositions were measured and the relative melt flow rate and Izodimpact values calculated as described above. The relative melt flow rateand percent change from the expected Izod impact value for eachcomposition are reported in Tables 8 and 9 below. Some of the testedcompositions containing a compatibilizing agent according to theinvention did not completely fracture during the Izod impact testing.These compositions are reported in Tables 8 and 9 as “Non-Break” and“Partial.” Since these “Non-Break” and “Partial” break samples did notcompletely fracture, the Izod impact value of the samples could not bequantified using this test. In other words, the impact strength of thesesamples exceeded the limits of the test. Since the impact strength ofthe “Non-Break” and “Partial” break samples could not be quantifiedusing the same test as the unmodified polypropylene copolymer (i.e., thevis-broken copolymer without a compatibilizing agent), a relative Izodimpact value could not be calculated. Nevertheless, the fact thatsamples did not fracture completely during the test reveals that theimpact strength of the polymer was significantly increased.

TABLE 7 Compatibilizing agent identification numbers (Compound ID) andcompound structures. Compound ID Compound Structure  1

 2

 3

 4

 5

 6

 7

 9

10

12

13

14

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

44

45

46

47

48

49

50

51

52

53

54

59

60

61

62

63

64

65

66

67

68

69

70

73

78

80

83

84

85

86

87

88

89

90

91

94

95

96

98

100 

101 

102 

TABLE 8 Results for compounds loaded at a ratio of 1 mole compound per 1mole of peroxide bonds. Change in Izod Impact Sample Compound IDRelative MFR over Expected Value 3-1 1 2.57 100.6% 3-2 2 3.27 82.7% 3-33 3.52 38.5% 3-4 4 3.16 82.0% 3-5 5 4.62 −4.0% 3-6 6 3.90 20.8% 3-7 73.68 16.3% 3-8 9 3.37 24.8% 3-9 10 4.50 7.8% 3-10 12 3.72 48.2% 3-11 134.67 3.6% 3-12 14 3.67 61.3% 3-13 16 3.34 29.0% 3-14 17 3.38 19.2% 3-1518 4.64 −0.6% 3-16 19 2.32 85.5% 3-17 20 1.93 74.3% 3-18 21 3.96 14.7%3-19 22 3.58 33.7% 3-20 23 3.85 48.6% 3-21 24 3.70 27.7% 3-22 25 3.893.7% 3-23 26 1.48 68.5% 3-24 27 3.77 18.1% 3-25 28 2.22 54.5% 3-26 293.58 22.6% 3-27 30 4.12 15.3% 3-28 31 2.83 18.9% 3-29 32 3.03 39.6% 3-3033 2.60 45.9% 3-31 34 2.89 32.7% 3-32 35 1.65 88.2% 3-33 36 3.25 102.4%3-34 37 2.30 82.4% 3-35 38 3.10 40.9% 3-36 39 3.02 24.7% 3-37 40 2.3860.5% 3-38 41 2.63 80.6% 3-39 42 4.18 67.9% 3-40 44 5.62 5.2% 3-41 455.47 20.3% 3-42 46 4.59 9.6% 3-43 47 3.46 77.0% 3-44 48 4.46 35.1% 3-4549 3.84 75.7% 3-46 50 3.63 96.5% 3-47 51 3.66 42.2% 3-48 52 2.91 116.4%3-49 53 3.24 70.4% 3-50 54 5.26 20.8% 3-51 59 4.63 18.8% 3-52 60 4.50−2.5% 3-53 61 4.43 26.4% 3-54 63 2.67 98.9% 3-55 64 1.99 97.4% 3-56 652.71 105.9% 3-57 66 3.82 38.8% 3-58 67 3.32 101.6% 3-59 68 2.30 102.7%3-60 69 2.46 155.7% 3-61 70 4.44 50.1% 3-62 73 3.67 33.5% 3-63 78 4.7077.8% 3-64 80 4.64 −21.6% 3-65 83 1.73 100.6% 3-66 84 3.63 43.2% 3-67 852.73 76.9% 3-68 86 1.88 69.3% 3-69 87 2.84 75.3% 3-70 88 2.62 106.5%3-71 89 4.01 33.9% 3-72 90 2.94 68.1% 3-73 91 3.08 28.0% 3-74 94 3.0568.2% 3-75 95 2.41 110.2% 3-76 96 2.17 105.2% 3-77 98 5.52 12.3% 3-78100 3.40 79.9% 3-79 101 3.14 80.7% 3-80 102 1.61 Non-Break

TABLE 9 Results for compounds loaded at a ratio of 2 moles of compoundper 1 mole of peroxide bonds. Change in Izod Impact Sample Compound IDRelative MFR over Expected Value 3-101 1 1.61 Non-Break 3-102 2 2.06113.4% 3-103 3 2.80 46.1% 3-104 4 2.42 94.5% 3-105 5 3.79 19.7% 3-106 62.54 36.6% 3-107 7 2.97 24.9% 3-108 9 2.53 27.0% 3-109* 10 3.43 20.0%3-110 12 3.07 49.5% 3-111 13 3.84 10.6% 3-112 14 2.60 30.0% 3-113 163.05 34.2% 3-114 17 2.70 25.6% 3-115 18 3.96 8.4% 3-116 19 1.79Non-Break 3-117 20 1.91 67.5% 3-118 21 3.91 33.3% 3-119 22 3.08 40.1%3-120 23 2.58 59.1% 3-121 24 3.23 35.5% 3-122 25 3.29 7.8% 3-123 26 1.19Non-Break 3-124 27 2.96 33.5% 3-125 28 1.22 58.8% 3-126 29 2.91 37.5%3-127 30 3.15 22.5% 3-128 31 2.23 31.5% 3-129 32 2.82 35.0% 3-130 332.14 95.7% 3-131 34 2.66 45.2% 3-132 35 1.55 84.5% 3-133 36 2.84 132.4%3-134 37 1.87 124.0% 3-135 38 2.40 48.3% 3-136 39 2.30 50.4% 3-137 412.25 87.8% 3-138 42 3.79 116.3% 3-139 44 5.16 5.5% 3-140 45 5.05 8.4%3-141 46 4.50 16.7% 3-142 47 2.99 134.6% 3-143 48 3.98 39.6% 3-144 492.83 68.1% 3-145 50 3.50 116.6% 3-146 51 2.45 52.1% 3-147 52 2.21Partial 3-148 53 2.49 89.4% 3-149 54 4.68 30.9% 3-150 59 3.11 14.4%3-151 60 3.82 0.5% 3-152 61 3.43 56.3% 3-153 62 3.72 48.5% 3-154 63 2.26110.7% 3-155 64 1.68 111.3% 3-156 65 2.11 113.0% 3-157 66 3.52 51.3%3-158 67 2.49 104.5% 3-159 68 1.50 Partial 3-160 69 1.96 Partial 3-16170 3.08 64.4% 3-162 73 2.99 52.3% 3-163 78 2.82 89.7% 3-164 80 4.67−7.2% 3-165 83 1.81 82.7% 3-166 84 3.07 58.1% 3-167 85 2.14 Non-Breakand Partial 3-168 86 1.93 51.7% 3-169 87 2.37 95.8% 3-170 88 1.86 110.9%3-171 89 3.72 38.4% 3-172 90 2.51 106.4% 3-173 91 2.41 31.3% 3-174 942.50 81.8% 3-175 95 1.66 124.3% 3-176 96 1.79 104.6% 3-177 98 4.67 25.1%3-178 100 2.54 91.0% 3-179 101 2.54 98.1% 3-180 102 1.35 Non-Break*Compound 10 was loaded in Sample 3-109 at a molar ratio of 4 moles ofcompound per 1 mole of peroxide bonds.

The results set forth in Tables 8 and 9 demonstrate that compositionscontaining compatibilizing agents according to the invention can achievesignificant increases in the melt flow rate as compared to the virgin,non-vis-broken resin. These results also demonstrate that compositionscontaining compatibilizing agents according to the invention can achievemeasurable (and in many cases significant) increases in Izod impactstrength of the polymer. The significance of the increase can varydepending on the loading of the compatibilizing agent, but eachcompatibilizing agent according to the invention was able to achieve atleast a 5% increase over the expected Izod impact value at one of thetested loadings, which is believed to be a commercially significantincrease. Many of the compatibilizing agents were capable of producinggreater than 15% increases over the expected Izod impact value. Further,a comparison of the data for Compound ID 60 and Compound ID 80 show thatstructurally similar compounds (i.e., compounds that are structurallysimilar to the compatibilizing agent of the invention but do not possessall of the defined features) do not yield significant increases over theexpected Izod impact value. Indeed, Compound ID 80 actually led to ameasurable decrease over the expected Izod impact value.

EXAMPLE 4

The following example demonstrates the production of a modifiedheterophasic polyolefin composition, created by melt mixing apolypropylene homopolymer, a polyolefin elastomer, an organic peroxideand the compatibilizing agent of the present invention.

In particular, a 2 dg/min polypropylene homopolymer (TotalPetrochemicals 3276), 20 w/w % of a polyolefin elastomer (Engage™ 7467from The Dow Chemical Company), an organic peroxide (Varox DBPHavailable from R.T. Vanderbilt Company) and Compound ID 1 were meltmixed and tested. The results were compared to the heterophasicpolyolefin composition created when peroxide only was present and whenneither the peroxide nor the compatibilizing agent were present.

The loadings of the peroxide and Compound ID 1 are listed in Table 10.Each of the polymer blend compositions was mixed, extruded, andinjection molded according to the above procedure. The bars were thensubjected to melt flow rate and Izod impact testing described above.

TABLE 10 Heterophasic polyolefin composition formed during melt mixingSample C.S. 4A C.S. 4B 4A Peroxide Loading (ppm) — 1000  1500 AdditiveLoading (Molar — — 1:1 ratio Additive: O—O) Additive Loading (ppm) — —1490 Melt Flow Rate (g/10 min)  2.2 21  10 Izod impact at 23° C. (J/m)341 95 380 (Partial) (Complete) (Partial) Izod impact at −30° C. (J/m)22.5 36  37

The blend of the polypropylene homopolymer and the polyolefin elastomerwithout either the peroxide or the compatibilizing agent (C.S. 4A),exhibits partial break Izod impact behavior at 23° C., but has anundesirably low melt flow rate. When peroxide is added to the blend(C.S. 4B), the melt flow rate increases substantially, but the 23° C.Izod Impact Strength is undesirably reduced from a partial break to 95J/m. Surprisingly, when Compound ID 1 is added at a 1490 ppm loading, asdemonstrated in Sample 4A, the melt flow rate remains high and the 23°C. Izod Impact strength exhibits partial break behavior. The inventiveSample 4A achieves a desirable balance of high melt flow rate and highIzod Impact Strength performance.

EXAMPLE 5

The following example demonstrates the production of compositions andperformance enhancements achieved through the incorporation of acompatibilizing agent according to the invention into a high-impactheterophasic polypropylene copolymer.

The resin used for these samples was an 18 MFR high-impact, heterophasicpolypropylene copolymer, Pro-Fax SG702 (LyondellBasell Industries) whichhad approximately 25% xylene solubles. The compositions consisted of theingredients listed in Table 11.

TABLE 11 High-impact heterophasic polypropylene copolymer ComponentAmount LyondellBasell Pro-Fax SG702 Balance Primary antioxidant(Irganox ® 1010) 500 ppm Secondary antioxidant (Irgafos ® 168) 1000 ppm Calcium stearate 400 ppm Varox DBPH See Table 12 Compound ID 1 See Table12 Irganox ® 1010 is available from BASF Irgafos ® 168 is available fromBASF Varox DBPH is available from R. T. Vanderbilt Company

Each of the compositions was compounded by blending the components in aclosed container for approximately one minute. The compositions werethen melt compounded on a Prism TSE-16-TC co-rotating, fullyintermeshing, parallel, twin-screw extruder with a 16 mm screw diameterand a length/diameter ratio of 25:1. The barrel temperature of theextruder was ramped from approximately 195° C. to approximately 215° C.,and the screw speed was set at approximately 500 rpm. The extrudate (inthe form of a strand) for each polypropylene copolymer composition wascooled in a water bath and subsequently pelletized.

The pelletized compositions were then used to form bars by injectionmolding the compositions on an Arburg 40 ton injection molder having a25.4 mm diameter screw. The barrel temperature of the injection molderwas approximately 200 to 220° C., and the mold temperature wasapproximately 25° C. The resulting bars measured approximately 127 mmlong, approximately 12.7 mm wide, and approximately 3.2 mm thick. Thebars were then subjected to the impact tests described below.

The notched Charpy impact strength for the bars was measured accordingto ASTM method D6110-10. The notched Charpy impact strength was measuredat +23° C. on bars that had been conditioned at either +23° C. or −30°C. The melt flow rate (MFR) was determined according to (ASTM D1238) at230° C. with a load of 2.16 kg for polypropylene. The resulting changein melt flow rate and Charpy impact at 23° C. and −30° C. is listed inTable 12.

TABLE 12 Performance in high-impact, heterophasic polypropylenecopolymer Sample C.S. 5A C.S. 5B 5A Peroxide Loading (ppm) — 250 1000 Additive Loading (Molar — — 1:1 ratio Additive: O—O) Additive Loading(ppm) — — 991 Melt Flow Rate (g/10 min) 17  40  40 Charpy impact at 23°C. (J/m) 159 111 Non-Break Charpy impact at −30° C. (J/m) 90  56 115

The compositions resulting from the addition of 250 ppm of organicperoxide only (C.S. 5B) demonstrate that as the peroxide is added to thehigh-impact polypropylene copolymer, the melt flow rate increasessignificantly, but the Charpy impact at 23° C. and −30° C. decreasesundesirably. The use of Compound ID 1 with 1000 ppm peroxide shown inSample 5A demonstrates a desired increase in melt flow rate while theCharpy impact performance at 23° C. exhibits highly desirable non-breakbehavior and the Charpy impact performance at −30° C. is also increased.

EXAMPLE 6

The following example demonstrates the production of heterophasicpolymer compositions according to the invention.

The heterophasic polymer compositions used in this example were a blendin which the polypropylene homopolymer was a minority component. Inother words, the polypropylene hompolymer was the discrete phase of theheterophasic polymer composition. The polymer blends of the presentinvention consisted of a polyolefin elastomer (Engage™ 8842 from The DowChemical Company) and a 2 dg/min polypropylene homopolymer (TotalPetrochemicals 3276) in a ratio of 3:1 w/w. 1,000 ppm of an organicperoxide (Varox DBPH available from R.T. Vanderbilt Company) andCompound ID 52 were added to this polymer blend. The loadings of theperoxide and Compound ID 52 are listed in Table 13, with the balance ofthe blend being the polyolefin elastomer and polypropylene homopolymer.The results were compared to the heterophasic polyolefin compositioncreated when peroxide only was present (C.S. 6B) and when neither theperoxide nor the compatibilizing agent were present (C.S. 6A).

Each of the compositions was compounded by blending the components in aclosed container for approximately one minute. The compositions werethen melt compounded on a Prism TSE-16-TC co-rotating, fullyintermeshing, parallel, twin-screw extruder with a 16 mm screw diameterand a length/diameter ratio of 25:1. The barrel temperature of theextruder was ramped from approximately 195° C. to approximately 215° C.,and the screw speed was set at approximately 500 rpm. The extrudate (inthe form of a strand) for each polyolefin blend composition was cooledin a water bath and subsequently pelletized. The pelletized compositionswere then compression molded on a 12 ton Carver Press at a platentemperature of 230° C. and a holding pressure of approximately 6 tonsfor approximately 4 minutes into a sheet that was approximately 6″ wide,6″ long, and 0.047″ thick. ASTM Type IV dog bone specimens were then diecut from these compression-molded sheets. The tensile properties for theASTM Type IV dog bones were measured according to ASTM method D638 usingan MTS Q-Test-5 with a crosshead speed of 20.0 in/min.

TABLE 13 Performance of Polyolefin Blends Sample C.S. 6A C.S. 6B 6A 6B6C Peroxide Loading (ppm) — 1000 1000 1000 1000 Additive Loading (Molar— — 1:2 1:1 2:1 ratio Additive: O—O) Additive Loading (ppm) — — 948 28445692 Tensile Strength at 4.4 4.1 5.3 7.0 9.3 Yield (MPa) Elongation atYield (%) 531 740 599 609 846

The composition comprising peroxide only (no compatibilizing agent)demonstrates that when peroxide is added to a polyolefin blendcontaining a 3:1 w/w ratio of polyolefin elastomer to polypropylenehomopolymer, the tensile yield strength decreases and the elongation atyield increases. When Compound ID 52 is added to this blend, as shown inSamples 6A-6C, the tensile strength at yield increases significantly.The combination of Compound ID 52 with peroxide also increases theelongation at yield over the unmodified resin. Sample 6C alsodemonstrates that the addition of the compatibilizing agent at a 1:2molar ratio results in an elongation at yield that is higher than withperoxide only.

EXAMPLE 7

The following example demonstrates the production of a modifiedmasterbatch composition as described above and the physical propertyimprovements that can be achieved through the addition of such amodified masterbatch composition to a heterophasic polyolefincomposition.

Three modified masterbatch compositions were produced. ComparativeSample 7-MB (C.S. 7-MB) was made by melt compounding a polypropylenecopolymer with a peroxide as a vis-breaking agent. Samples 7A-MB and7B-MB were made by melting compounding the same polypropylene copolymerwith a peroxide as a vis-breaking agent and 2-furylidene malononitrile(Compound ID 1) as a compatibilizing agent. The general formulation forthese samples is set forth in Table 14.

TABLE 14 Modified masterbatch formulations. Component LoadingPolypropylene copolymer Balance (LyondellBasell Pro-Fax SG702) Peroxide(Varox DBPH) See Table 15 Compatibilizing Agent (MN-1) See Table 15

Each of the compositions listed in Table 14 was mixed and extrudedaccording to the procedure described above.

TABLE 15 Modified masterbatch compositions. Sample C.S. 7-MB 7A-MB 7B-MBPeroxide Loading (ppm) 500 1,500 3,000 Additive Loading (Molar — 1:1 1:1ratio Additive: O—O) Additive Loading (ppm) — 2,960 5,920

Three heterophasic polymer compositions were produced by adding themodified masterbatch compositions described above to a polypropylenecopolymer. Comparative Sample 7A (C.S. 7A) was the unmodifiedpolypropylene copolymer. Comparative Sample 7B (C.S. 7B) was made bycompounding the unmodified polypropylene copolymer with ComparativeSample 7-MB (C.S. 7-MB). Sample 7A was made by compounding the sameunmodified polypropylene copolymer with Sample 7A-MB, and Sample 7B wasmade by compounding the same unmodified polypropylene copolymer withSample 7B-MB. The general formulation for these samples is set forth inTables 16 and 17.

TABLE 16 Heterophasic polypropylene copolymer formulations with modifiedmasterbatches. Component Loading Polypropylene copolymer Balance (ExxonPP7414) C.S. 7-MB See Table 17 7A-MB See Table 17 7B-MB See Table 17

Each of the compositions listed in Table 17 was mixed, extruded, andinjection molded according to the procedures described above. Theresulting bars were then subjected to melt flow rate and Izod impacttesting as described above.

TABLE 18 Performance in medium-impact, heterophasic polypropylenecopolymer Sample C.S. 7A C.S. 7B 7A 7B C.S. 7-MB (%) — 10   — — 7A-MB(%) — — 10 — 7B-MB (%) — — — 10 Melt Flow Rate (g/10 min) 20.7 22.9 23.222.6 Izod impact at 23° C. (J/m) 94.7 88.6 109.0 115.8

The data set forth in Table 18 demonstrate that a modified masterbatchaccording to the invention (e.g., a modified masterbatch made by meltcompounding a heterophasic polymer with a vis-breaking agent and acompatibilizing agent) can be melt compounded into an unmodifiedheterophasic polymer, thereby significantly improving the impactstrength of the heterophasic polymer. For example, the data for C.S. 7Bshow that melt compounding the vis-broken masterbatch C.S. 7-MB into theunmodified heterophasic polymer does not appreciably affect the impactstrength of the polymer. In fact, the Izod impact strength for C.S. 7Bwas actually lower than the Izod impact strength of the unmodifiedpolymer. By way of contrast, the data for Samples 7A and 7B show thatmelt compounding the unmodified heterophasic polymer with the modifiedmasterbatch compositions Sample 7A-MB and Sample 7B-MB increases theimpact strength of the polymer by as much as 22%. This increase inimpact strength is particularly valuable because it demonstrates thatimproved heterophasic polymer compositions can be produced withoutdirectly adding the vis-breaking agent and/or compatibilizing agent tothe target heterophasic polymer. Direct addition of such additives canbe difficult in certain settings, such as compounding facilities andinjection molding facilities. However, such facilities routinely utilizemasterbatch compositions. Therefore, such facilities could readilyachieve the physical property improvements described herein through theuse of a modified masterbatch composition as described above.

All references, including publications, patent applications, andpatents, cited herein are hereby incorporated by reference to the sameextent as if each reference were individually and specifically indicatedto be incorporated by reference and were set forth in its entiretyherein.

The use of the terms “a” and “an” and “the” and similar referents in thecontext of describing the subject matter of this application (especiallyin the context of the following claims) are to be construed to coverboth the singular and the plural, unless otherwise indicated herein orclearly contradicted by context. The terms “comprising,” “having,”“including,” and “containing” are to be construed as open-ended terms(i.e., meaning “including, but not limited to,”) unless otherwise noted.Recitation of ranges of values herein are merely intended to serve as ashorthand method of referring individually to each separate valuefalling within the range, unless otherwise indicated herein, and eachseparate value is incorporated into the specification as if it wereindividually recited herein. All methods described herein can beperformed in any suitable order unless otherwise indicated herein orotherwise clearly contradicted by context. The use of any and allexamples, or exemplary language (e.g., “such as”) provided herein, isintended merely to better illuminate the subject matter of theapplication and does not pose a limitation on the scope of the subjectmatter unless otherwise claimed. No language in the specification shouldbe construed as indicating any non-claimed element as essential to thepractice of the subject matter described herein.

Preferred embodiments of the subject matter of this application aredescribed herein, including the best mode known to the inventors forcarrying out the claimed subject matter. Variations of those preferredembodiments may become apparent to those of ordinary skill in the artupon reading the foregoing description. The inventors expect skilledartisans to employ such variations as appropriate, and the inventorsintend for the subject matter described herein to be practiced otherwisethan as specifically described herein. Accordingly, this disclosureincludes all modifications and equivalents of the subject matter recitedin the claims appended hereto as permitted by applicable law. Moreover,any combination of the above-described elements in all possiblevariations thereof is encompassed by the present disclosure unlessotherwise indicated herein or otherwise clearly contradicted by context.

What is claimed is:
 1. A heterophasic polymer composition comprising:(a) a propylene polymer phase comprising propylene polymers selectedfrom the group consisting of polypropylene homopolymers and copolymersof propylene and up to 50 wt. % of one or more comonomers selected fromthe group consisting of ethylene and C₄-C₁₀ α-olefin monomers; (b) anethylene polymer phase comprising ethylene polymers selected from thegroup consisting of ethylene homopolymers and copolymers of ethylene andone or more C₃-C₁₀ α-olefin monomers; and (c) a compatibilizing agent,the compatibilizing agent comprising (i) an acyclic carbon-carbon doublebond having a first carbon atom and a second carbon atom, (ii) anelectron withdrawing group directly bonded to the first carbon atom inthe acyclic carbon-carbon double bond, and (iii) a second carbon-carbonmultiple bond in conjugation with the acyclic carbon-carbon double bond,wherein the second carbon-carbon multiple bond is linked to the acycliccarbon-carbon double bond through the second carbon atom.
 2. Theheterophasic polymer composition of claim 1, wherein the secondcarbon-carbon multiple bond is a carbon-carbon double bond.
 3. Theheterophasic polymer composition of claim 1, wherein the compatibilizingagent is selected from the group consisting of compounds conforming tothe structure of Formula (I)

wherein R₁ is selected from the group consisting of aryl groups,substituted aryl groups, heteroaryl groups, substituted heteroarylgroups, and groups conforming to the structure of Formula (V)

where R₅ and R₆ are independently selected from the group consisting ofhydrogen, alkyl groups, substituted alkyl groups, cycloalkyl groups,substituted cycloalkyl groups, aryl groups, substituted aryl groups,heteroaryl groups, and substituted heteroaryl groups or R₅ and R₆ can becombined to form a cyclic structure; and x is an integer selected fromthe group consisting of 0, 1, and 2; R₂ is selected from the groupconsisting of hydrogen, halogens, alkyl groups, substituted alkylgroups, aryl groups, substituted aryl groups, heteroaryl groups, andsubstituted heteroaryl groups; R₃ and R₄ are independently selected fromthe group consisting of hydrogen, alkyl groups, substituted alkylgroups, cycloalkyl groups, substituted cycloalkyl groups, cyano groups,nitro groups, and groups conforming to a structure of Formula (VI),(VII), (VIII), or (IX)

where R₇ and R₉ are independently selected from the group consisting ofalkyl groups, substituted alkyl groups, cycloalkyl group, substitutedcycloalkyl groups, aryl groups, substituted aryl groups, heteroarylgroups, and substituted heteroaryl groups; R₈ is selected from the groupconsisting of hydrogen, alkyl groups, substituted alkyl groups,cycloalkyl group, substituted cycloalkyl groups, aryl groups,substituted aryl groups, heteroaryl groups, and substituted heteroarylgroups; provided, for groups conforming to the structure of Formula(VIII), R₇ and R₉ can be combined to form a cyclic structure; andprovided at least one of R₃ and R₄ is selected from the group consistingof cyano groups, nitro groups, and groups conforming to a structure ofFormula (VI), (VII), (VIII), or (IX).
 4. The heterophasic polymercomposition of claim 1, wherein the compatibilizing is selected from thegroup consisting of compounds conforming to the structure of Formula (X)

wherein R₁₀ is selected from the group consisting of arenediyl groups,substituted arenediyl groups, heteroarenediyl groups, substitutedheteroarenediyl groups, and groups conforming to the structure ofFormula (XV)

where R₁₅ is selected from the group consisting of a direct bond betweenR₁₆ and R₁₇, an oxygen atom, an alkanediyl group, and a substitutedalkanediyl group; R₁₆ and R₁₇ are independently selected from the groupconsisting of arenediyl groups, substituted arenediyl groups,heteroarenediyl groups, and substituted heteroarenediyl groups; R₁₁,R₁₂, R₁₃, and R₁₄ are independently selected from the group consistingof hydrogen, alkyl groups, substituted alkyl groups, cycloalkyl groups,substituted cycloalkyl groups, cyano groups, nitro groups, and groupsconforming to a structure of Formula (VI), (VII), (VIII), or (IX)

where R₇ and R₉ are independently selected from the group consisting ofalkyl groups, substituted alkyl groups, cycloalkyl group, substitutedcycloalkyl groups, aryl groups, substituted aryl groups, heteroarylgroups, and substituted heteroaryl groups; R₈ is selected from the groupconsisting of hydrogen, alkyl groups, substituted alkyl groups,cycloalkyl group, substituted cycloalkyl groups, aryl groups,substituted aryl groups, heteroaryl groups, and substituted heteroarylgroups; provided, for groups conforming to the structure of Formula(VIII), R₇ and R₉ can be combined to form a cyclic structure; andprovided at least one of R₁₁ and R₁₂ and at least one of R₁₃ and R₁₄ isselected from the group consisting of cyano groups, nitro groups, andgroups conforming to a structure of Formula (VI), (VII), (VIII), or(IX).
 5. The heterophasic polymer composition of claim 1, wherein thecompatibilizing is selected from the group consisting of compoundsconforming to the structure of Formula (XX)

wherein R₂₀ is a divalent linking group; R₂₁ and R₂₂ are selected fromthe group consisting of cyano groups, nitro groups, and groupsconforming to a structure of Formula (VI), (VII), (VIII), or (IX)

where R₇ and R₉ are independently selected from the group consisting ofalkyl groups, substituted alkyl groups, cycloalkyl group, substitutedcycloalkyl groups, aryl groups, substituted aryl groups, heteroarylgroups, and substituted heteroaryl groups; R₈ is selected from the groupconsisting of hydrogen, alkyl groups, substituted alkyl groups,cycloalkyl group, substituted cycloalkyl groups, aryl groups,substituted aryl groups, heteroaryl groups, and substituted heteroarylgroups; provided, for groups conforming to the structure of Formula(VIII), R₇ and R₉ can be combined to form a cyclic structure; R₂₃, R₂₄,R₂₅, and R₂₆ are independently selected from the group consisting ofhydrogen, alkyl groups, substituted alkyl groups, cycloalkyl groups,substituted cycloalkyl groups, aryl groups, substituted aryl groups,heteroaryl groups, substituted heteroaryl groups, and groups conformingto the structure of Formula (V)

where R₅ and R₆ are independently selected from the group consisting ofhydrogen, alkyl groups, substituted alkyl groups, cycloalkyl groups,substituted cycloalkyl groups, aryl groups, substituted aryl groups,heteroaryl groups, and substituted heteroaryl groups or R₅ and R₆ can becombined to form a cyclic structure; and x is an integer selected fromthe group consisting of 0, 1, and 2; provided at least one of R₂₃ andR₂₄ and at least one of R₂₅ and R₂₆ is selected from the groupconsisting of aryl groups, substituted aryl groups, heteroaryl groups,substituted heteroaryl groups, and groups conforming to the structure ofFormula (V).
 6. The heterophasic polymer composition of claim 5, whereinR₂₀ is a group conforming to the structure of Formula (XXV)

wherein R₂₇ is selected from the group consisting of an oxygen atom,—N(H)—, and —N(R₂₉)—, where R₂₉ is selected from the group consisting ofalkyl groups, substituted alkyl groups, cycloallkyl groups, andsubstituted cycloalkyl groups; and R₂₈ is selected from the groupconsisting of alkanediyl groups and cycloalkanediyl groups.
 7. Theheterophasic polymer composition of claim 5, wherein R₂₀ is a groupconforming to the structure of Formula (XXX)

wherein R₃₀ is selected from the group consisting of alkanediyl groupsand cycloalkanediyl groups; R₃₁ is selected from the group consisting ofan oxygen atom, —N(H)—, and —N(R₂₉)—, where R₂₉ is selected from thegroup consisting of alkyl groups, substituted alkyl groups, cycloallkylgroups, and substituted cycloalkyl groups; and R₃₂ is selected from thegroup consisting of arenediyl groups, substituted arenediyl groups,heteroarenediyl groups, and substituted heteroarenediyl groups.
 8. Theheterophasic polymer composition of claim 1, wherein the ethylenepolymers are selected from the group consisting of ethylene-propyleneelastomers, ethylene-butene elastomers, ethylene-hexene elastomers,ethylene-octene elastomers, and mixtures thereof.
 9. The heterophasicpolymer composition of claim 1, wherein the ethylene polymer comprisesfrom 5 to 80 wt. % of the heterophasic polyolefin polymer composition,based on the total weight of propylene polymers and ethylene polymers inthe composition.
 10. The heterophasic polymer composition of claim 9,wherein the ethylene polymer comprises about 5 to 60 wt. % of theheterophasic polyolefin polymer composition, based on the total weightof propylene polymers and ethylene polymers in the composition.
 11. Theheterophasic polymer composition of claim 1, wherein the propylenecontent of the propylene polymer phase is 80 wt. % or greater.
 12. Theheterophasic polymer composition of claim 1, wherein the ethylenepolymer phase is a discontinuous phase in the heterophasic polyolefinpolymer composition.
 13. The heterophasic polymer composition of claim1, wherein the compatibilizing agent is present in the heterophasicpolyolefin polymer composition in a concentration of from 10 ppm to 5wt. %, based on the total weight of the composition.
 14. A heterophasicpolymer composition comprising a continuous phase comprisingpolypropylene polymers selected from the group consisting ofpolypropylene homopolymers and copolymers of propylene and up to 80 wt.% of one or more comonomers selected from the group consisting ofethylene and C₄-C₁₀ α-olefin monomers and a discontinuous phasecomprising elastomeric ethylene copolymers having an ethylene content offrom 8 to 90 wt. % selected from the group consisting of copolymers ofethylene and one or more C₃-C₁₀ α-olefin monomers, provided that thepropylene content of the propylene polymer phase is greater than thepropylene content of the ethylene polymer phase, wherein the compositionfurther comprises propylene polymers bonded to ethylene copolymers by acompatibilizing agent, wherein the compatibilizing agent comprises (i)an acyclic carbon-carbon double bond having a first carbon atom and asecond carbon atom, (ii) an electron withdrawing group directly bondedto the first carbon atom in the acyclic carbon-carbon double bond, and(iii) a second carbon-carbon multiple bond in conjugation with theacyclic carbon-carbon double bond, wherein the second carbon-carbonmultiple bond is linked to the acyclic carbon-carbon double bond throughthe second carbon atom.
 15. The heterophasic polymer composition ofclaim 14, wherein the discontinuous phase comprises from 5 to 35 wt. %of the heterophasic polyolefin polymer composition, based on the weightof propylene polymers and ethylene copolymers in the composition. 16.The heterophasic polymer composition of claim 14, wherein the ethylenecopolymer comprising the discontinuous phase has an ethylene content offrom 8 to 80 wt. %.
 17. The heterophasic polymer composition of claim14, wherein the heterophasic polyolefin polymer composition comprisesfrom 5 to 30 wt. % ethylene, based on the total weight of propylenepolymers and ethylene copolymers in the composition.
 18. Theheterophasic polymer composition of claim 14, wherein the heterophasicpolyolefin polymer composition is obtained by operating in at least twopolymerization stages.
 19. The heterophasic polymer composition of claim14, wherein the propylene content of the propylene polymer phase is 80wt. % or greater.
 20. The heterophasic polymer composition of claim 14,wherein the compatibilizing agent is present in the heterophasicpolyolefin polymer composition in a concentration of from 10 ppm to 5wt. %, based on the total weight of the composition.
 21. A heterophasicpolyolefin polymer composition obtained by the process comprising thesteps of: (a) providing a propylene polymer phase comprising propylenepolymers selected from the group consisting of polypropylenehomopolymers and copolymers of propylene and up to 50 wt. % of one ormore comonomers selected from the group consisting of ethylene andC₄-C₁₀ α-olefin monomers and an ethylene polymer phase comprisingethylene polymers selected from the group consisting of ethylenehomopolymers and copolymers of ethylene and one or more C₃-C₁₀ α-olefinmonomers provided that the ethylene content of the ethylene polymerphase is at least 8 wt. %, (b) providing a compatibilizing agent,wherein the compatibilizing agent comprises (i) an acyclic carbon-carbondouble bond having a first carbon atom and a second carbon atom, (ii) anelectron withdrawing group directly bonded to the first carbon atom inthe acyclic carbon-carbon double bond, and (iii) a second carbon-carbonmultiple bond in conjugation with the acyclic carbon-carbon double bond,wherein the second carbon-carbon multiple bond is linked to the acycliccarbon-carbon double bond through the second carbon atom; and (c) mixingthe propylene polymer phase, the ethylene polymer phase and thecompatibilizing agent in the presence of free carbon radicals, wherebypropylene polymers are bonded to ethylene polymers by thecompatibilizing agent, and whereby the propylene polymer phase and theethylene polymer phase form a heterophasic composition.
 22. Theheterophasic polymer composition of claim 21, wherein the propylenepolymer phase, the ethylene polymer phase and the compatibilizing agentare mixed in the presence of free carbon radicals by melt compounding,and the composition is heterophasic at 25° C.
 23. The heterophasicpolymer composition of claim 21, wherein the propylene polymer phase isthe continuous phase and the propylene content of the propylene polymerphase is 80 wt. % or greater, and the ethylene polymer phase is thediscontinuous phase and the ethylene polymers have an ethylene contentof from 8 to 80 wt. % and are selected from the group consisting ofcopolymers of ethylene and one or more C₃-C₁₀ α-olefin monomers.
 24. Amethod of making a heterophasic polyolefin polymer composition, themethod comprising the steps of: (a) providing a propylene polymer phasecomprising propylene polymers selected from the group consisting ofpolypropylene homopolymers and copolymers of propylene and up to 50 wt.% of one or more comonomers selected from the group consisting ofethylene and C₄-C₁₀ α-olefin monomers, and an ethylene polymer phasecomprising ethylene polymers selected from the group consisting ofethylene homopolymers and copolymers of ethylene and one or more C₃-C₁₀α-olefin monomers provided that the ethylene content of the ethylenepolymer phase is at least 8 wt. %, (b) providing a compatibilizingagent, wherein the compatibilizing agent comprises (i) an acycliccarbon-carbon double bond having a first carbon atom and a second carbonatom, (ii) an electron withdrawing group directly bonded to the firstcarbon atom in the acyclic carbon-carbon double bond, and (iii) a secondcarbon-carbon multiple bond in conjugation with the acycliccarbon-carbon double bond, wherein the second carbon-carbon multiplebond is linked to the acyclic carbon-carbon double bond through thesecond carbon atom; and (c) mixing the propylene polymer phase, theethylene polymer phase and the compatibilizing agent, in the presence offree carbon radicals, whereby the compatibilizing agent reacts withpropylene polymers and ethylene polymers thereby bonding propylenepolymers to ethylene polymers, and whereby the propylene polymer phaseand the ethylene polymer phase form a heterophasic composition.
 25. Themethod of claim 24, wherein the propylene polymer phase, the ethylenepolymer phase and the compatibilizing agent are mixed in the presence offree carbon radicals by melt compounding, and the composition isheterophasic at 25° C.
 26. The method of claim 24, wherein the propylenepolymer phase is the continuous phase and the propylene content of thepropylene polymer phase is 80 wt. % or greater, and the ethylene polymerphase is the discontinuous phase and the ethylene polymers have anethylene content of from 8 to 80 wt. % and are selected from the groupconsisting of copolymers of ethylene and one or more C₃-C₁₀ α-olefinmonomers.
 27. The method of claim 24, wherein the polypropylene phaseand the ethylene phase are provided to the mixture as a heterophasicimpact copolymer obtained by operating in at least two polymerizationstages.
 28. The method of claim 24, wherein the compatibilizing agent ispresent in the heterophasic polyolefin polymer composition in aconcentration of from 10 ppm to 5 wt. %, based on the total weight ofthe composition, and wherein a reaction between the unsaturated bond ofthe compatibilizing agent and the ethylene polymer is conducted in thepresence of a free radical generator selected from the group consistingof organic peroxides incorporating one or more peroxide bonds, and thecompatibilizing agent and the organic peroxide are present in a ratio ofmoles of compatibilizing agent to molar equivalents of peroxide bonds of1:10 to 10:1.